(3E,5E)-1-palmitoyl-3,5-bis(pyridin-4-ylmethylene)piperidin-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3E,5E)-1-palmitoyl-3,5-bis(pyridin-4-ylmethylene)piperidin-4-one
• 英文别名: (3E,5E)-1-hexadecanoyl-3,5-bis(pyridin-4-ylmethylidene)piperidin-4-one
• 化学式: C₃₃H₄₅N₃O₂
• 分子量: 515.739
• InChiKey: PCNXGJHQZYIEOE-AMLXCYGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氧代哌啶酮盐酸盐 在 盐酸 、 溶剂黄146 、 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成 (3E,5E)-1-palmitoyl-3,5-bis(pyridin-4-ylmethylene)piperidin-4-one
  参考文献：
  名称：

  Investigation of fatty acid conjugates of 3,5-bisarylmethylene-4-piperidone derivatives as antitumor agents and human topoisomerase-IIα inhibitors

  摘要：

  A series of five 3,5-bisarylidene-4-piperidones designed as analogs of curcumin and their twenty five fatty acid conjugates were synthesized as candidate anticancer agents. The fatty acid conjugates were designed for efficient delivery of these compounds at the targeted cancer sites. The cytostatic potential of these compounds was evaluated against three representative cancer cell lines namely murine leukemic L1210 cells, and human T-lymphocyte CEM cells and cervical HeLa cells. Most compounds were found to exhibit significant anti-cancer activity in vitro. QSAR studies indicated electrophilicity of these compounds towards cellular nucleophiles may have a key role to play in their cytostatic activity. Representative compounds were also tested for topoisomerase II alpha inhibitory potential, which indicated strong catalytic inhibition of the enzyme in vitro. The data showed that the fatty acid conjugates also possessed robust antioxidant activity in multiple analyses. This study also indicated that these compounds prompted significantly lower cellular damage in human fibroblasts than a currently used cancer drug sorafenib in vitro. The wide spectrum of anticancer action, supplemented with antioxidant potential along with non-toxic manifestations, certainly augment the anticancer candidacy of the novel fatty acid conjugates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.042

文献信息

• Investigation of fatty acid conjugates of 3,5-bisarylmethylene-4-piperidone derivatives as antitumor agents and human topoisomerase-IIα inhibitors
  作者：Elizabeth Potter、Mamta Jha、Khushwant S. Bhullar、H.P. Vasantha Rupasinghe、Jan Balzarini、Amitabh Jha

  DOI：10.1016/j.bmc.2014.12.042

  日期：2015.2

  A series of five 3,5-bisarylidene-4-piperidones designed as analogs of curcumin and their twenty five fatty acid conjugates were synthesized as candidate anticancer agents. The fatty acid conjugates were designed for efficient delivery of these compounds at the targeted cancer sites. The cytostatic potential of these compounds was evaluated against three representative cancer cell lines namely murine leukemic L1210 cells, and human T-lymphocyte CEM cells and cervical HeLa cells. Most compounds were found to exhibit significant anti-cancer activity in vitro. QSAR studies indicated electrophilicity of these compounds towards cellular nucleophiles may have a key role to play in their cytostatic activity. Representative compounds were also tested for topoisomerase II alpha inhibitory potential, which indicated strong catalytic inhibition of the enzyme in vitro. The data showed that the fatty acid conjugates also possessed robust antioxidant activity in multiple analyses. This study also indicated that these compounds prompted significantly lower cellular damage in human fibroblasts than a currently used cancer drug sorafenib in vitro. The wide spectrum of anticancer action, supplemented with antioxidant potential along with non-toxic manifestations, certainly augment the anticancer candidacy of the novel fatty acid conjugates. (C) 2014 Elsevier Ltd. All rights reserved.